Synthesis of isoflavene-thiosemicarbazone hybrids and evaluation of their anti-tumor activity

Bioorg Med Chem Lett. 2017 Jun 1;27(11):2454-2458. doi: 10.1016/j.bmcl.2017.04.002.

Eugene M H Yee ¹, Miriam B Brandl ², David StC Black ¹, Orazio Vittorio ², Naresh Kumar ³

Affiliations

1 School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia.
2 Children's Cancer Institute Australia, Lowy Cancer Research Centre, UNSW, Randwick, NSW, Australia; Australian Centre for NanoMedicine, University of New South Wales, Sydney, NSW 2052, Australia.
3 School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia. Electronic address: n.kumar@unsw.edu.au.

PMID: 28408225 DOI: 10.1016/j.bmcl.2017.04.002

Abstract

Phenoxodiol is an isoflavene with potent anti-tumor activity. In this study, a series of novel mono- and di-substituted phenoxodiol-thiosemicarbazone hybrids were synthesized via the condensation reaction between phenoxodiol with thiosemicarbazides. The in vitro anti-proliferative activities of the hybrids were evaluated against the neuroblastoma SKN-BE(2)C, the triple negative breast Cancer MDA-MB-231, and the glioblastoma U87 Cancer cell lines. The mono-substituted hybrids exhibited potent anti-proliferative activity against all three Cancer cell lines, while the di-substituted hybrids were less active. Selected mono-substituted hybrids were further investigated for their cytotoxicity against normal MRC-5 human lung fibroblast cells, which identified two hybrids with superior selectivity for Cancer cells over normal cells as compared to phenoxodiol. This suggests that mono-substituted phenoxodiol-thiosemicarbazone hybrids have promising potential for further development as anti-cancer agents.

Keywords

Anti-cancer; Isoflavene; Phenoxodiol; Thiosemicarbazone.

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